Reaction Steps
13-Hydroxymethyldibenzo(a,c)fluorene (215.2 mg, 0.727 mmol) was dissolved in acetic anhydride (5 ml). To this solution was added one drop of sulfuric acid (2M). The reaction mixture was stirred for 30 min. A white precipitate was obtained which was filtered and washed with water (150 ml). The solid was finally dried to constant weight over P2O5 in a vacuum desiccator to afford 13-acetoxymethyldibenzo(a,c)fluorene as a white solid, (206.3 mg, 84%); m.p. 135-136° C.; (Found: C, 84.9; H, 5,33; C24H18O2 requires: C, 85.2; H, 5.33%; t.l.c. Rf(D) 0.57; Rf(E) 0.68; νmax (CH2C2) 3030 (CH stretching, aryl) 2980, 2920 (CH stretching, alkyl) 1735 (CO, ester), 1610, 1600, 1570 (aromatic rings) cm−1; λmax 366 (1184), 338 (25160), 322 (27528), 265 (52688), 246 (53020) nm; δH (CDCl3, 200 MHz), 8.86-8.69 (3H, m aromatic), 9.38 (1H, d, 3J=7.9 Hz, aromatic), 8.30-8.25 (1H, m, aromatic), 7.78-7.35 (7H, m, aromatic), 5.16 (1H, dxd, 3Ja,c=4.1 Hz, 2Ja,b=10.8 Hz, Ha, CH2), 4.56 (1H, dxd, 3Jc,a=4.1 Hz, 3Jc,b=9.3 Hz, Hc), 3.76 (1H, dxd, 2Jb,a=10.8 Hz, 3Jb,c=9.3 Hz, Hb, CH2), 2.17 (3H, s, CH3); δC (CDCl3, 50 MHz) 171.0 (CO, ester), 146.7, 142.1, 138.7, 134.8 131.1, 130.1, 128.7, 128.6 (quaternary aromatic C's), 127.6, 127.0, 126.8, 126.2, 126.1, 125.7, 124.9, 124.8, 124.3, 123.4, 123.3, 122.9 (aromatic CH's), 67.3 (CH2), 46.5 (CH), 20.9 (CH3); m/z (EI) 338, 277, 265, 139, 43.
